NEW APPROACH TO THE SYNTHESIS OF 2,2':5',2''-TERTHIOPHENE-5,5''- AND 2,2':5',2'':5'',2'''-QUATERTHIOPHENE-5,5'''-DICARBOXYLIC ACIDS

Authors

  • Анастасия С. Костюченко Omsk State Technical University, 11 Mira Ave., Omsk 644050 F. M. Dostoyevsky Omsk State University, 55a Mira Ave., Omsk 644077, Russia
  • Евгений Б. Ульянкин Omsk State Technical University, 11 Mira Ave., Omsk 644050 F. M. Dostoyevsky Omsk State University, 55a Mira Ave., Omsk 644077, Russia
  • Антон Л. Шацаускас Omsk State Technical University, 11 Mira Ave., Omsk 644050 F. M. Dostoyevsky Omsk State University, 55a Mira Ave., Omsk 644077, Russia
  • Владислав Ю. Шувалов Omsk State Technical University, 11 Mira Ave., Omsk 644050 F. M. Dostoyevsky Omsk State University, 55a Mira Ave., Omsk 644077, Russia
  • Александр С. Фисюк Omsk State Technical University, 11 Mira Ave., Omsk 644050 F. M. Dostoyevsky Omsk State University, 55a Mira Ave., Omsk 644077, Russia

DOI:

https://doi.org/10.1007/4676

Keywords:

2, 2', 5', 2'', 5'', 2'''-quaterthiophene-5, 5'''-dicarboxylic acids, 2''-terthiophene-5, 5''-dicarboxylic acids, esters of 3-alkyl- 2, 2'-bithiophene-5-carboxylic acids

Abstract

The reaction of bromosuccinimide with esters of 3-substituted 2,2'-bithiophene-5-carboxylic acids was used to obtain their 5'-bromo derivatives, which were further converted to esters of 3,3'''-disubstituted 2,2':5',2'':5'',2'''-quaterthiophene-5,5'''-dicarboxylic acids by heating in DMF with catalytic amounts of Pd(PPh3)4. Ester of 3-decyl-2,2'-bithiophene-5-carboxylic acid was acylated at the С-5' position with lauroyl chloride in the presence of SnCl4, producing the respective ketone that was used in Vilsmeier–Haack reaction (DMF, POCl3). The 3-chloroacrylaldehyde derivative that was thus obtained was further used in reaction with ethyl thioglycolate in the presence of sodium ethoxide, giving ester of 3,3''-decyl-2,2':5',2''-terthiophene-5,5''-dicarboxylic acid. Alkaline hydrolysis of the obtained esters led to the corresponding 2,2':5',2'':5'',2'''-quaterthiophene-5,5'''- and 2,2':5',2''-terthiophene-5,5''-dicarboxylic acids.

Authors: Anastasia S. Kostyuchenko, Evgeny B. Ulyankin, Anton L. Shatsauskas, Vladislav Yu. Shuvalov, Alexander S. Fisyuk*

Author Biographies

Анастасия С. Костюченко, Omsk State Technical University, 11 Mira Ave., Omsk 644050 F. M. Dostoyevsky Omsk State University, 55a Mira Ave., Omsk 644077, Russia

старший преподаватель кафедры "Химическая технология и биотехнология"

Евгений Б. Ульянкин, Omsk State Technical University, 11 Mira Ave., Omsk 644050 F. M. Dostoyevsky Omsk State University, 55a Mira Ave., Omsk 644077, Russia

аспирант каф. органическая химия

Антон Л. Шацаускас, Omsk State Technical University, 11 Mira Ave., Omsk 644050 F. M. Dostoyevsky Omsk State University, 55a Mira Ave., Omsk 644077, Russia

аспирант кафедры "Химическая технология и биотехнология"

Владислав Ю. Шувалов, Omsk State Technical University, 11 Mira Ave., Omsk 644050 F. M. Dostoyevsky Omsk State University, 55a Mira Ave., Omsk 644077, Russia

аспирант каф. "Химическая технология и биотехнология"

Александр С. Фисюк, Omsk State Technical University, 11 Mira Ave., Omsk 644050 F. M. Dostoyevsky Omsk State University, 55a Mira Ave., Omsk 644077, Russia

Заведующий кафедрой органической химии ОмГУ им. Ф.М. Достоевского, заведующий лабораторией "Новые органические материалы" ОмГТУ, д.х.н., профессор.

Published

2018-12-12

Issue

Section

Original Papers